Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of aldehydes to nitrostyrenes

被引:363
作者
Wang, W [1 ]
Wang, J [1 ]
Li, H [1 ]
机构
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
关键词
aldehydes; asymmetric catalysis; Michael addition; nitroalkenes; organocatalysts;
D O I
10.1002/anie.200461959
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Just can't get enough: The highly versatile pyrrolidine sulfonamide organocatalyst 1, which has been used in α-aminoxylation and Mannich-type reactions, also mediates diastereo- and enantioselective Michael addition reactions of aldehydes and ketones to nitroolefins (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1369 / 1371
页数:3
相关论文
共 46 条
[31]   Proline-catalyzed asymmetric reactions [J].
List, B .
TETRAHEDRON, 2002, 58 (28) :5573-5590
[32]   Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins [J].
List, B ;
Pojarliev, P ;
Martin, HJ .
ORGANIC LETTERS, 2001, 3 (16) :2423-2425
[33]   Asymmetric aminocatalysis [J].
List, B .
SYNLETT, 2001, (11) :1675-1686
[34]   Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents [J].
List, B .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :548-557
[35]   Direct asymmetric organocatalytic Michael reactions of α,α-disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products [J].
Mase, N ;
Thayumanavan, R ;
Tanaka, F ;
Barbas, CF .
ORGANIC LETTERS, 2004, 6 (15) :2527-2530
[36]   Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines [J].
Melchiorre, P ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4151-4157
[37]   Enamine-based organocatalysis with proline and diamines: The development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-Alder reactions [J].
Notz, W ;
Tanaka, F ;
Barbas, CF .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :580-591
[38]   Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts [J].
Okino, T ;
Hoashi, Y ;
Takemoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12672-12673
[39]   The enantioselective organocatalytic 1,4-addition of electron-rich benzenes to α,β-unsaturated aldehydes [J].
Paras, NA ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7894-7895
[40]   New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation [J].
Paras, NA ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4370-4371